How does Truewind handle the "art" of bookkeeping in their system?

Accounting software companies have tried to capture the context through rules. Let's say you swipe your credit card on something called Slack, and then the memo says a bunch of words and numbers, and the word Slack in there. We both know what that is. But if you send an ACH wire to John Matthews, I don't know who John Matthews is, you do. You tell me it's your marketing contractor. Going forward, I will note that's your marketing contractor, but not all the context. 

Companies have continually tried to do it by letting you save rules. If a transaction that comes in as Gusto, it is going to be saved as payroll, Slack is saved as software, John Matthews, it'll be saved as a marketing contractor, which, in theory should work. And yet, anyone who uses QuickBooks will all agree that the rules feature is at best 50% accurate.

Even with Gusto, one transaction is $4,000 and it says Gusto, you know that's payroll, but another transaction is $40 and it says it's Gusto, that's not payroll, that's a software tool that you pay for. So little nuances like that. 

In terms of the business context piece, I think this is where the holy grail ultimately comes in. You know how there are some of those knowledge management AI companies, where they want to take all your meeting notes, or take all the activities that happen for a week, and generate a weekly PowerPoint for your all-hands meeting?

I think the holy grail of accounting ultimately comes from capturing all the other context that happens. Now, I also hesitate with saying that because you're going to end up capturing like 97% of things that don't matter. 

This is a complicated problem.

I was talking with a CRO who was trying to win a really big sales contract, and he started getting really, really creative with his contract, which would make a very meaningful impact on how we track ARR, but also how we measure things for accounting. These are the nuances that rules-based software just can't do. And even with AI today, I wouldn't feel entirely comfortable with it. But just seeing how fast AI is growing, I think that's where we need to start looking ahead and think, ‘all right, we may not be able to capture it with 99% confidence today, but maybe in one to two years, the tech will be there.’ And these are the types of contexts that we can start capturing and making the bookkeepers' lives easier.